Where To Stay In The Berkshires

Planning a trip to The Berkshires? Ah, then you’re in for a treat. Imagine this: a dreamy patch of New England, where mountains meet eclectic culture and country charm rolls out like a warm, flannel blanket by a crackling fire. Just the thought makes you want to dig out your coziest sweater, right? The Berkshires have been pulling people in for generations—artists, dreamers, even the occasional city-dweller craving fresh air (and maybe a slice of solitude). From Gilded Age mansions to quaint inns straight from a storybook, here’s your go-to guide for the best hotels in this charming corner of Massachusetts.

1. Blantyre, Lenox – For The Classic Romantic

Stepping into Blantyre is like taking a glorious step back in time, somewhere around the Downton Abbey era—minus the rigid social structure, of course. This grand estate is all polished mahogany, roaring fireplaces, and rooms so plush they practically dare you to leave them. Perfect for romance or for anyone who wants to pretend they’re a fancy aristocrat (because who doesn’t?), Blantyre’s gardens, fine dining, and spa are fit for a weekend of decadence and a little daydreaming. Just be warned: You may find yourself sipping tea with a posh accent by Day 2. Perfect for: Romantic getaways, lovers of grand history, and those who always wish they were at a fancy garden party.

2. The Red Lion Inn, Stockbridge – Historical Setting

An icon in Stockbridge, The Red Lion Inn practically oozes nostalgia—yet somehow manages to keep things fresh. This isn’t just any old hotel; it’s the oldest continuously operating inn in the U.S., folks. (Yes, it’s that old.) But before you worry about creaky floors and ghost sightings, think instead of lively common rooms, an eccentric collection of antiques, and live music in the tavern most nights. This place is steeped in history, yet feels like it’s been dusted with whimsy and charm. Stock up on some Berkshire tales to regale your friends back home. Perfect for: History buffs, old souls, and fans of a good yarn (and a really good New England clam chowder).

3. The Inn at Kenmore Hall, Richmond – Your Dreamy, Storybook Cottage Once a 1792 farmhouse, The Inn at Kenmore Hall is now a charming bed and breakfast that’s cozied up on ten acres of rolling countryside. With period furnishings, wood-beamed ceilings, and floors that creak just the right amount, this inn offers a warmth that feels like a genuine escape from the everyday. Breakfast here is an event in itself—homemade pastries, fresh jams, and strong coffee by the fire. Kenmore Hall might make you wonder if the city life was ever really for you. Perfect for: Couples, solo travelers seeking peace, and breakfast enthusiasts.

4. Miraval Berkshires Resort & Spa, Lenox – Wellness Wonderland

Miraval isn’t just a resort; it’s a sanctuary for anyone looking to shed their stress like an old coat and walk away feeling reborn. With a wellness philosophy that promises more “ahhh” moments than you can count, Miraval offers everything from meditation classes to forest bathing (yes, it’s a thing). Add in plush accommodations and a spa that could melt away a year’s worth of stress, and you’ve got yourself a little oasis of serenity right in the heart of the Berkshires. Perfect for: Wellness seekers, yoga aficionados, and the perpetually stressed.

5. Devonfield Inn, Lee – The Quintessential Country Retreat

Imagine a picturesque country home with blue shutters, acres of gardens, and a swing that practically calls your name. That’s Devonfield Inn, where the setting is as New England as apple pie. The rooms are sweet and cozy, the atmosphere relaxed and unpretentious, and the views? Unmatched. Bonus: In the fall, the foliage here is postcard-perfect, so don’t forget your camera. Perfect for: Families, leaf-peepers, and fans of classic Americana.

6. The Porches Inn at MASS MoCA, North Adams – Quirky, Artsy Vibes

If you’re more the type to skip the spa and head straight for the art museum, The Porches Inn is your place. Right across from MASS MoCA, this inn is all about that funky, artsy vibe, with rooms that playfully blend vintage décor with modern flair. A former millworker’s row of houses has been transformed into eclectic suites, complete with retro furnishings, contemporary art, and a heated pool open year-round. You’ll leave with more than just some fabulous Instagram shots—expect a heart full of creative inspiration too. Perfect for: Artists, musicians, and free spirits who love a creative twist on the classic inn.

7. Canyon Ranch, Lenox – The Ultimate Retreat

Canyon Ranch is where you go to escape, reboot, and, well, live your best life. From fitness classes to a nutritionist on-site, they’re here to bring a holistic boost to your soul. And yes, there’s a spa, but this isn’t your basic spa—it’s all about transformation and balance. Sure, it’s a bit on the pricey side, but isn’t wellness worth it? Perfect for: Health enthusiasts, wellness junkies, and anyone who wants to get serious about self-care.

The Takeaway? From woodsy retreats to the most luxurious spots, The Berkshires have a little something for everyone. So grab a warm drink, settle in by the fire, and let these beautiful hotels lure you in. Whatever you choose, you’ll leave feeling like you’ve had a little taste of New England magic

What to Expect

Thinking about a Berkshires getaway? Picture this: mornings that begin with mountain mist rolling across golden fields, quaint towns where every coffee shop feels like the “one,” and days that stretch into cozy evenings by the fire. The Berkshires, nestled in western Massachusetts, has long been New England’s beloved retreat, drawing everyone from writers and artists to hikers and those just craving a break from city life. It’s the kind of place where you can do everything or nothing at all—and feel pretty good about it either way.

Why Choose The Berkshires?
The Berkshires blend high culture with natural beauty in a way that few places can. Museums like MASS MoCA, the Clark Art Institute, and the Norman Rockwell Museum offer something for every art lover. Then there’s Tanglewood, an iconic summer destination that turns into a world-class concert venue, attracting both casual listeners and serious classical music fans. And if you’re not here to take in culture? Head outdoors! Hiking trails crisscross every peak and valley, from Monument Mountain to the Appalachian Trail, offering views that make the climbs more than worth it.

A Taste of Berkshires Towns
Each town has its own personality. Lenox is a touch luxurious, with its refined inns, spas, and that lingering scent of history. Stockbridge, on the other hand, feels almost like a Norman Rockwell painting—quaint, timeless, and welcoming, with just enough quirk to keep things interesting. Great Barrington mixes that rural, small-town vibe with surprisingly eclectic dining and shopping, perfect for those who like their weekends with a side of discovery. And then there’s North Adams, a magnet for the artsy crowd, where post-industrial architecture and art installations mesh with craft breweries and cafes.

When to Go?
Fall, of course, is when the region truly shines, with foliage that can’t be beaten. Spring is lovely too, with fresh blooms and hiking trails just warming up. Winters in the Berkshires are magical, especially if you’re here for skiing or snowshoeing—and there’s no shortage of cozy inns to hibernate in after a day out. Summer has its own draw: lush greenery, cool mountain breezes, and a calendar full of events and festivals.

Where to Stay?
Whether you’re looking for a five-star retreat or a charming B&B, the Berkshires has you covered. For those who appreciate luxury with a slice of history, places like Blantyre or Wheatleigh in Lenox have just the right amount of grandeur. Art lovers may want to try The Porches Inn in North Adams, where retro style meets contemporary flair right across from MASS MoCA. And if you’re looking for a holistic wellness escape, Miraval Berkshires in Lenox and Canyon Ranch promise an immersive experience in relaxation and self-care.

Where To Stay In The Berkshires